Keeping time-sheets is habit that I’ve developed over the past 10 years. Time-sheets are amazing. They give me confidence in my work and help me overcome my chronic impostor syndrome.

Why do you do?

Logging the time I spend on any job lets me:

  1. know when I am spending appropriate time on work
  2. know the timeline I can potentially complete future work
  3. bill for my time appropriately (freelance, or day job)

Appropriate Time

It took me several jobs over as many years to learn some things about myself.:

  • I am obsessive.
  • I want to feel I've done a good job.
  • I feel anxiety when work is not done.
  • I feel anxiety when others are expecting work from me.

If the above behaviors combine I will sink too much time into almost any job to attempt to avoid my irrational feelings.

Tracking time lets me see the hours I've put into my work. It gives me the freedom to stand up and walk away when I have put in the time I've agreed to. It also shows me historic data on projects I completed (survived).

This performs a sort-of judo on my brain and allows it to relax. I did enough work today; more things will get done tomorrow.


I am paid to write code, design systems, take photographs, etc. It is almost always subjective, creative work. It never takes exactly the same amount of time to do a job but in broad strokes like things take about the same time.

Bosses, stakeholders, clients, co-workers, managers all want to know know when a job will be done. There are many religions on how to measure how long creative work can and should take. I've been part of several of these methodologies but all leave my work anxieties untamed.

I have found that the most important control I have in my work is what I agree to. These agreements are made less irrational and emotional by time tracking.

I know two important facts from time tracking. The maximum and minimum amount of time any job has lasted in the past.

Since I've tracked my time for almost a decade I can use hind-sight to provide context for future work (don't worry the benefits arrives much quicker than a decade).

Most jobs are similar enough that they can be grouped into a type of projects. From there you can see the fastest you have ever completed a job and the longest it has ever taken.

Here is the superpower; never agree to do a job faster than the fastest time you have completed a similar job. This lets you have honest conversations with those requesting work too quickly.

If a job truly is new and your past time tracking isn't relevant you can have honest conversations with folks around that too; this is new for me I can't tell you how long it will take.

Billing & Negotiations

Freelance in my work means billings. Day job means negotiations. I essentially use the two concepts interchangeably.

Time is a fixed variable. I only get 24hrs a day. Set your acceptable work/life balance where you see fit but it will be less than 24hrs a day.

Working backwards from there you can tell what your time is worth.

  1. I know what type of jobs I am willing to do.
  2. I have examples of the fastest & slowest timelines for those jobs.

From there my agreements with others are simple:

  1. I am willing to do the job asked or I am not.
  2. I know if the proposed deadlines appears unreasonable based on past experience or it is new.
  3. If a timeline feels unreasonable I say that I am not comfortable doing the amount of work in that time.

This leads to frank, honest discussions about what is being asked. It also brings conflict to the beginning of the process instead the end. These conversations can get uncomfortable. But they are way worse if you agree to work and miss the timeline.

This isn't a down-to-the-minute scientific process. I don't tell a boss no if something is off by 15min. However if someone is asking me to do a job I know I have never finished faster than 2 weeks I cannot agree to have it done by tomorrow morning.

How does one do?

If you have never tracked time, and want to give it a shot, I suggest a spreadsheet.

You sheet should look like this:

client task date start time stop time
Tom dig tunnel 2018-07-08 09:30 10:30
Dick chop wood 2018-07-08 10:30 12:00
Harry hide dirt 2018-07-09 09:30 16:30
Tom dig tunnel 2018-07-10 09:30 14:00
Tom dig tunnel 2018-07-10 10:30 12:00
Harry hide dirt 2018-07-13 10:30 15:45

This is enough data to help find trends later. If you track this for ~1month you should see if it is providing you value or not. I have found that the few times I've let myself slip from my habit that I regret it.

How do you do?

Currently I am using Tyme 2. It has a macOS and iOS app and syncs over iCloud.

It has one feature I love and is worth $$$ to me. If you close or log out of your Mac it will prompt you on the next log in; asking if you want to stop the timer when you logged out. This solves a problem of mine; not stopping timers in the evening or because I shut my laptop in a hurry.

Another money feature for me is the Statistics view. It is a bar graph showing the work across the day, week, month, or year. It is a simple way to see if I am over or under expected working hours. This can be accomplished on your own in a spreadsheet application using pivot tables and mental elbow-grease.

This app also doesn't hold my data hostage. I can export a CSV (tabular data) to move into a spreadsheet or some future app.

My setup in Tyme 2 is as follows:

  • Category for day job

    • Project per project
    • 1 Task Admin for each project ( I don't find further granularity necessary at my current day job)
  • Category for freelance (paid or pro bono)

    • Project per client

      • Task per job

My workflow is to turn on a timer for the task I am on; turn it off when I'm done working (or when it reminds you in the morning).

I look at the Statistics view daily to see that I am getting as close to a 40 hour work week at the day job as possible.

I review freelance totals when it is time to bill each client or have a talk about a project going too long.

Closing Time

Like any productivity related thought–technology there is potential for endless fussing and fiddling. However I have found using simple tools, it has given me confidence in my ability to do work sustainably. I recommend you give it a try, if only for a time 😉.